IT’S EMBARRASSING to admit in a public forum that I failed at retirement. But I’m doing so—because I think people can learn from me, and thereby avoid making the same mistakes.
I spent my entire 38-year career in the banking industry. Naturally, I learned a lot about money and investing. I helped thousands of clients save for their own retirement. On top of that, my wife is an investment advisor.
But despite all that knowledge and expertise—and having enough money to retire comfortably—I still managed to find my way into retirement hell.

I BEGAN WRITING this article after reading a Facebook group’s page filled with derogatory comments about seniors and technology. The comments related to seniors’ inability to use a smartphone. Talk about stereotyping. The fact is, some of us seniors are addicted to technology—at least the nontechnical part.

For example, I recently went shopping and forgot something vital. No, I had my face mask. What I was missing was my smartphone. Smart is an appropriate word because,

I’VE HAD SOME dreadful jobs in my life. I spent one summer putting metal plates under a huge press for eight hours a day. Once the plates were in the right position, I’d push some buttons that would cause the press to crash down and shape the metal into something useful.
The goal was to work fast because that meant more pay. Some of the workers disabled the safety features so they could produce more widgets and earn extra money.

“SHOULD YOU BUY an annuity from Social Security?” That’s the title of a paper released by Boston College’s Center for Retirement Research (CRR) in May 2012. It’s one of the best articles I’ve ever read about the Social Security claiming decision—and it’s had a big impact on my thinking.
Most of us know what an income annuity is: You hand over a sum of money and, in return, receive a check every month for the rest of your life or for a specified period of time.

THE MUCH-DEBATED 4% rule—which I wrote about back in July—is a popular way to think about portfolio withdrawals in retirement. But it isn’t the only way. Another approach, called the bucket system, is also worth understanding. Below is some background.
What is the bucket system? As its name suggests, an investor divides his or her portfolio into multiple containers. Each container, or bucket, is then assigned a different role.
The most popular implementation of the bucket system involves three containers: The first is earmarked for a year or two of spending and is held entirely in cash.

I RECENTLY HAD LUNCH with four friends I’ve known since the seventh grade. Because of the pandemic, this was the first time we’d all seen each other in more than a year. Every time we’re together, I’m reminded of how important my friends were in helping me start a new life when I left home for the first time. Our continuing support for each other is probably the reason we’ve stayed close for 57 years.

ON THE SURFACE, Social Security seems straightforward: During our working years, we pay into the system. Then, when we’re older, the government sends a check every month for life.
But scratch the surface and you’ll find that Social Security offers a number of additional benefits. Among them: a benefit for spouses. This can be highly valuable, but the rules around it are complex and very specific. Consider, for example, the late talk show host Johnny Carson.

THE 4% RULE IS ONE of the best-known ideas in personal finance. But is it really a rule? And does it apply to you?

Let’s start at the beginning. The father of the 4% rule is a financial planner named William Bengen. Back in the early 1990s, he became frustrated with the prevailing rules of thumb for retirement planning. He found them too informal and set out to develop a more rigorous approach. The question he sought to answer: What percentage of a portfolio could a retiree safely withdraw each year?

I RECENTLY WROTE about how my wife and I downsized to our beach home. It had long been a dream of ours and we’re thrilled it came about. Right after the move, we climbed on a plane and experienced another common dream of retirees—living in an exotic tropical paradise.
We visited our son, daughter-in-law, grandson and their Boston terrier in Nosara, Costa Rica. Nosara is a beautiful village and resort area carved out of the jungle on Nicoya Peninsula,

I JUST REVIEWED my Social Security earnings record. It brings back memories. For instance, it shows I earned $105 in 1959 when I was age 16 and working after school in the city library for 75 cents an hour. I’ve paid Social Security taxes every year since, though in 2020 they were based on earnings of just $2,333 and I was counted as self-employed. That darn blogging money.

Here’s something to put matters in perspective: Over 64 years,

MY RELATIONSHIP with money is complicated. I want to get the best value for our dollars, so I spend a lot of time comparison shopping. Other people hunt for bargains. I go on long safaris.
My frugality and comparison shopping have served Jim and me well. In our double-income household, we managed to save 50% of our combined pay—basically living on one income and saving the rest. That, coupled with some lucky breaks, propelled us to early retirement.

A 156-YEAR-OLD newspaper company filed for reorganization in bankruptcy court last year. The company said it just couldn’t come up with the millions it owed to its pension plan. Some 24,000 current and future retirees were promised payments from that plan—and I’m one of them.
This is the story of what happened to our benefits after the pension plan failed.
For 10 years, I was lucky enough to cover Washington, DC, as a newspaper reporter.

MANY PEOPLE TELL ME they need, say, $1 million or $2 million to retire, effectively equating retirement with a dollar amount. But there’s more to retirement than just the financial side. It’s a major turning point that will alter virtually all of our priorities—how we spend our days, how we interact with loved ones, what we care about and what we hope to achieve.

Even if we focus only on the financial side, we can’t sum up retirement with a single number.

LEAVING BEHIND fulltime work leaves a void. How will you fill it? In my semi-retirement, I’ve found four communities.
I grew up in Fort Worth, Texas, but moved throughout my career. Fifteen years ago, I returned to Texas and—as part of my relocation—”pioneered” working from home. I’ve spent the past few years reconnecting with classmates from elementary school through high school, meeting them individually for lunch and using Facebook to arrange annual mini-reunions. I’ve known some of these folks for more than 55 years.

RETIREMENT AT FIRST is fun and feels pretty good. No more setting an alarm. No more dealing with a long commute. No demanding work schedule that leaves you exhausted most evenings.
Best of all, no one is telling you what to do. You can sleep in or travel to all those places you dreamed about. You can golf as much as you like or spend lots of time with the grandkids.
You’re as free as a bird.